Real Estate Investment Properties for Sale in Oakland, MD

Looking for investment property in Oakland, MD with high ROI ?

Explore a variety of short-term homes & houses in Oakland, MD. Invest wisely with VRBO & Oakland, MD Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Investment Property for Sale in Oakland, MD

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
565 GLENDALE Road #306 Oakland, MD Experience the best of Deep Creek Lake living from this beautifully appointed studio loft ...	2 beds \| 1 baths \| 772 sq.ft.	$249,900	Airbnb cash on cash: 1.67% Traditional cash on cash: 5.25% Airbnb Rental Income: $1310 Traditional Rental Income: $1747 Airbnb ROI: 1.67% Traditional ROI: 5.25%
321 DEER PARK HOTEL Road Oakland, MD Double lots! Lot 4 & 5 of Hunting Ridge Estates will be sold together to bring up a total ...	3 beds \| 2 baths \| 2,476 sq.ft.	$399,900	Airbnb cash on cash: 0.64% Traditional cash on cash: 5.41% Airbnb Rental Income: $1309 Traditional Rental Income: $2692 Airbnb ROI: 0.64% Traditional ROI: 5.41%
256 JEFFREY Lane #28 Oakland, MD Looking for a beautifully updated condo at Deep Creek Lake? Welcome to 256 Jeffrey Lane #2...	3 beds \| 4 baths \| 1,838 sq.ft.	$464,900	Airbnb cash on cash: -0.11% Traditional cash on cash: 5.35% Airbnb Rental Income: $1309 Traditional Rental Income: $3281 Airbnb ROI: -0.11% Traditional ROI: 5.35%
638 GLENDALE Road Oakland, MD Spacious five-bedroom lakeview home offering the perfect blend of relaxation and warmth fr...	5 beds \| 3 baths \| 2,640 sq.ft.	$745,000	Airbnb cash on cash: 0.48% Traditional cash on cash: 2.49% Airbnb Rental Income: $2422 Traditional Rental Income: $3228 Airbnb ROI: 0.48% Traditional ROI: 2.49%
98 BEAR RUN Road Oakland, MD Make it your own! This 2-acre parcel comes with two additional parcels of 17.96 and 24.23 ...	3 beds \| 2 baths \| 1,080 sq.ft.	$550,000	Airbnb cash on cash: 0.16% Traditional cash on cash: 3.29% Airbnb Rental Income: $1309 Traditional Rental Income: $2510 Airbnb ROI: 0.16% Traditional ROI: 3.29%
25 SILVER TREE Lane Oakland, MD Beautiful lake access retreat located in the Silver Tree Landings community with an availa...	5 beds \| 4 baths \| 2,364 sq.ft.	$749,900	Airbnb cash on cash: 0.34% Traditional cash on cash: 1.81% Airbnb Rental Income: $2422 Traditional Rental Income: $2858 Airbnb ROI: 0.34% Traditional ROI: 1.81%
55 VILLAGE Drive #5 Oakland, MD Tucked in the Yellowstone Village community at Deep Creek Lake, "Dan's Mountain" is a char...	3 beds \| 3 baths \| 2,280 sq.ft.	$585,000	Airbnb cash on cash: -0.34% Traditional cash on cash: 3.66% Airbnb Rental Income: $1309 Traditional Rental Income: $3088 Airbnb ROI: -0.34% Traditional ROI: 3.66%
8956 OAKLAND SANG RUN Road Oakland, MD Welcome to The Wise Quack - our cozy cabin in the center of Deep Creek Lake activities...a...	3 beds \| 2 baths \| 1,064 sq.ft.	$219,900	Airbnb cash on cash: 2.54% Traditional cash on cash: 9.26% Airbnb Rental Income: $1309 Traditional Rental Income: $2302 Airbnb ROI: 2.54% Traditional ROI: 9.26%
467 PARADISE RIDGE Road Oakland, MD Panoramic mountain and lake views set the tone at this lake access home in Paradise Ridge,...	4 beds \| 4 baths \| 3,780 sq.ft.	$769,900	Airbnb cash on cash: -0.19% Traditional cash on cash: 2.84% Airbnb Rental Income: $2035 Traditional Rental Income: $3685 Airbnb ROI: -0.19% Traditional ROI: 2.84%
113 JUBB MEADOWS Lane Oakland, MD Luxury Estate just outside the town of Oakland. This 4-bed, 3.5 bath is situated on 9.72 a...	4 beds \| 4 baths \| 3,185 sq.ft.	$899,900	Airbnb cash on cash: -0.28% Traditional cash on cash: 1.83% Airbnb Rental Income: $2035 Traditional Rental Income: $3274 Airbnb ROI: -0.28% Traditional ROI: 1.83%
126 LEO FRIEND Road Oakland, MD Perched above the treetops with panoramic lake views, this three-level retreat blends comf...	4 beds \| 3 baths \| 2,235 sq.ft.	$499,900	Airbnb cash on cash: 1.41% Traditional cash on cash: 5.03% Airbnb Rental Income: $2035 Traditional Rental Income: $3200 Airbnb ROI: 1.41% Traditional ROI: 5.03%
449 S 3RD Street Oakland, MD Welcome to this beautifully updated 1901 home in the heart of downtown Oakland, where hist...	4 beds \| 2 baths \| 1,928 sq.ft.	$275,900	Airbnb cash on cash: 3.05% Traditional cash on cash: 7.55% Airbnb Rental Income: $2035 Traditional Rental Income: $2676 Airbnb ROI: 3.05% Traditional ROI: 7.55%
565 GLENDALE Road #106 B Oakland, MD Ground-floor end unit with lake views at Silver Tree Suites. This one-bedroom layout packs...	1 beds \| 1 baths \| N/A	$214,900	Airbnb cash on cash: 0.17% Traditional cash on cash: 6.58% Airbnb Rental Income: $835 Traditional Rental Income: $1813 Airbnb ROI: 0.17% Traditional ROI: 6.58%
328 STOOL ROCK Road Oakland, MD Designed and built for the sellers, this 4 bedroom, 2.5 bath home is a true showcase of cr...	4 beds \| 3 baths \| 1,860 sq.ft.	$545,000	Airbnb cash on cash: 1.11% Traditional cash on cash: 4.15% Airbnb Rental Income: $2035 Traditional Rental Income: $3055 Airbnb ROI: 1.11% Traditional ROI: 4.15%
157 JEFFREY Lane #21B Oakland, MD Nestled in the charming Traders Landing community, this delightful end-of-row townhouse of...	2 beds \| 1 baths \| 550 sq.ft.	$294,000	Airbnb cash on cash: 0.99% Traditional cash on cash: 2.87% Airbnb Rental Income: $1310 Traditional Rental Income: $1422 Airbnb ROI: 0.99% Traditional ROI: 2.87%
17921 GARRETT Highway Oakland, MD Charming and well-maintained, this 4-bedroom, 1.5-bath traditional home offers the perfect...	4 beds \| 2 baths \| 1,563 sq.ft.	$325,000	Airbnb cash on cash: 3.29% Traditional cash on cash: 7.12% Airbnb Rental Income: $2035 Traditional Rental Income: $2677 Airbnb ROI: 3.29% Traditional ROI: 7.12%
660 GLENDALE Road Oakland, MD Welcome to 660 Glendale Road - a luxury, mountain-chalet log home in the heart of Deep Cre...	5 beds \| 3 baths \| 2,592 sq.ft.	$1,100,000	Airbnb cash on cash: 0.09% Traditional cash on cash: 1.08% Airbnb Rental Income: $2422 Traditional Rental Income: $2839 Airbnb ROI: 0.09% Traditional ROI: 1.08%
127 PARADISE Heights Oakland, MD Beautifully renovated lake access log cabin with a deeded dock slip in a quiet cove with p...	3 beds \| 3 baths \| 2,240 sq.ft.	$1,075,000	Airbnb cash on cash: -0.83% Traditional cash on cash: 0.57% Airbnb Rental Income: $1309 Traditional Rental Income: $2308 Airbnb ROI: -0.83% Traditional ROI: 0.57%
565 GLENDALE Road #212A Oakland, MD Silver Tree Suites offers 350' of pristine shoreline at Deep Creek Lake with western expos...	1 beds \| 1 baths \| 527 sq.ft.	$175,000	Airbnb cash on cash: 0.64% Traditional cash on cash: 8.92% Airbnb Rental Income: $835 Traditional Rental Income: $1886 Airbnb ROI: 0.64% Traditional ROI: 8.92%
2725 STOCKSLAGER Road Oakland, MD Welcome to 2725 Stockslager Road, one of Deep Creek Lake's most coveted properties. This c...	5 beds \| 7 baths \| 5,376 sq.ft.	$2,350,000	Airbnb cash on cash: -1.21% Traditional cash on cash: 0.76% Airbnb Rental Income: $2422 Traditional Rental Income: $6125 Airbnb ROI: -1.21% Traditional ROI: 0.76%
163 MITCHELL Drive Oakland, MD Nestled in the charming Mitchell Manor community, this delightful split-level home offers ...	3 beds \| 3 baths \| 2,242 sq.ft.	$289,000	Airbnb cash on cash: 1.28% Traditional cash on cash: 9.98% Airbnb Rental Income: $1309 Traditional Rental Income: $3270 Airbnb ROI: 1.28% Traditional ROI: 9.98%
206 MAYHEW INN Road Oakland, MD Just 2.5 miles from the scenic Swallow Falls State Park, this charming 1-bedroom, 1-bath h...	1 beds \| 1 baths \| N/A	$224,900	Airbnb cash on cash: 0.56% Traditional cash on cash: 5.78% Airbnb Rental Income: $835 Traditional Rental Income: $1618 Airbnb ROI: 0.56% Traditional ROI: 5.78%
315 COOLIDGE Avenue Oakland, MD Well maintained brick rancher located in the heart of Oakland. This home offers a large ki...	3 beds \| 2 baths \| 1,600 sq.ft.	$269,500	Airbnb cash on cash: 1.44% Traditional cash on cash: 7.51% Airbnb Rental Income: $1309 Traditional Rental Income: $2447 Airbnb ROI: 1.44% Traditional ROI: 7.51%
531 GLENDALE Road #B302 Oakland, MD Experience effortless lakeside living at its finest in this spacious 2-bedroom, 1-bath uni...	2 beds \| 1 baths \| 887 sq.ft.	$339,900	Airbnb cash on cash: 0.69% Traditional cash on cash: 4.07% Airbnb Rental Income: $1310 Traditional Rental Income: $1981 Airbnb ROI: 0.69% Traditional ROI: 4.07%
415 NAZELROD Road Oakland, MD One of Garrett County's most unique and breathtaking mountain estates, this completely cus...	4 beds \| 5 baths \| 6,036 sq.ft.	$3,249,000	Airbnb cash on cash: -0.77% Traditional cash on cash: 0.43% Airbnb Rental Income: $2035 Traditional Rental Income: $5150 Airbnb ROI: -0.77% Traditional ROI: 0.43%
2311 BOY SCOUT Road Oakland, MD Experience the best of Deep Creek Lake living from this private waterfront retreat tucked ...	4 beds \| 3 baths \| 3,278 sq.ft.	$1,579,900	Airbnb cash on cash: -0.73% Traditional cash on cash: 0.8% Airbnb Rental Income: $2035 Traditional Rental Income: $3756 Airbnb ROI: -0.73% Traditional ROI: 0.8%
20160 GARRETT Highway #G507 Oakland, MD Experience lakefront living with this charming two-level condo at Will O the Wisp at Deep ...	2 beds \| 1 baths \| 912 sq.ft.	$389,000	Airbnb cash on cash: 0.57% Traditional cash on cash: 3.06% Airbnb Rental Income: $1310 Traditional Rental Income: $1811 Airbnb ROI: 0.57% Traditional ROI: 3.06%
1909 PYSELL CROSSCUT Road Oakland, MD Welcome to a private retreat on 4 acres with sweeping views and a large front yard, just m...	4 beds \| 5 baths \| 2,970 sq.ft.	$760,000	Airbnb cash on cash: 0.43% Traditional cash on cash: 5.13% Airbnb Rental Income: $2035 Traditional Rental Income: $4836 Airbnb ROI: 0.43% Traditional ROI: 5.13%
961 CEDAR Lane Oakland, MD Tucked away in the woods on 1.72 acres, this stunning 4-bedroom, 2.5-bath mountain retreat...	4 beds \| 3 baths \| 1,920 sq.ft.	$339,000	Airbnb cash on cash: 2.73% Traditional cash on cash: 7.39% Airbnb Rental Income: $2035 Traditional Rental Income: $2991 Airbnb ROI: 2.73% Traditional ROI: 7.39%
52 DAM VIEW Drive Oakland, MD Panoramic Lake views in the Bray Run community, just minutes from Deep Creek Lake, state p...	4 beds \| 6 baths \| 3,032 sq.ft.	$1,074,900	Airbnb cash on cash: -0.22% Traditional cash on cash: 3.97% Airbnb Rental Income: $2035 Traditional Rental Income: $5698 Airbnb ROI: -0.22% Traditional ROI: 3.97%
104 PINE TOP Trail Oakland, MD Here's your chance to purchase a cute Chalet with just about 7 acres. .This home and acrea...	3 beds \| 4 baths \| 1,596 sq.ft.	$425,000	Airbnb cash on cash: 0.3% Traditional cash on cash: 6.41% Airbnb Rental Income: $1309 Traditional Rental Income: $3334 Airbnb ROI: 0.3% Traditional ROI: 6.41%
5024 CRANESVILLE Road Oakland, MD Surrounded by 100+ Acres of Nature Conservancy conservation lands, on a 1.68-acre scenic h...	3 beds \| 3 baths \| 2,128 sq.ft.	$385,000	Airbnb cash on cash: 0.36% Traditional cash on cash: 6.4% Airbnb Rental Income: $1309 Traditional Rental Income: $3081 Airbnb ROI: 0.36% Traditional ROI: 6.4%
63 WALLMAN Road Oakland, MD Remodeled Rancher Near the North Branch Potomac River This charming 3-bedroom, 1-bath ranc...	3 beds \| 1 baths \| 816 sq.ft.	$164,000	Airbnb cash on cash: 3.89% Traditional cash on cash: 10.55% Airbnb Rental Income: $1309 Traditional Rental Income: $1944 Airbnb ROI: 3.89% Traditional ROI: 10.55%
181 JEFFREY Lane #23A Oakland, MD Discover comfort and convenience in this charming 2-bedroom, 1-bath unit ideally located i...	2 beds \| 1 baths \| 670 sq.ft.	$259,900	Airbnb cash on cash: 1.25% Traditional cash on cash: 3.95% Airbnb Rental Income: $1310 Traditional Rental Income: $1567 Airbnb ROI: 1.25% Traditional ROI: 3.95%
62 WILD TURKEY Court Oakland, MD Current new home construction project underway, but Builder not going to complete at this ...	4 beds \| 3 baths \| 2,390 sq.ft.	$249,000	Airbnb cash on cash: 4.91% Traditional cash on cash: 11.45% Airbnb Rental Income: $2035 Traditional Rental Income: $3044 Airbnb ROI: 4.91% Traditional ROI: 11.45%
4A MYSTIC CREEK Trail Oakland, MD Discover refined mountain-lake living in this new construction townhome at Mystic Creek on...	5 beds \| 5 baths \| 3,000 sq.ft.	$679,900	Airbnb cash on cash: 1.54% Traditional cash on cash: 5.97% Airbnb Rental Income: $2422 Traditional Rental Income: $4636 Airbnb ROI: 1.54% Traditional ROI: 5.97%
127 S Oakhall Dr Oakland, MD Welcome to this well maintained 4-bed, 2-bath ranch home on a generous corner lot in Oakla...	4 beds \| 2 baths \| 1,913 sq.ft.	$265,000	Airbnb cash on cash: 3.72% Traditional cash on cash: 8.91% Airbnb Rental Income: $2035 Traditional Rental Income: $2854 Airbnb ROI: 3.72% Traditional ROI: 8.91%
809 N St Oakland, MD 809 N St, Oakland, MD 21550 \| Single Family Residential	N/A beds \| N/A baths \| 792 sq.ft.	$63,000	Airbnb cash on cash: 2.84% Traditional cash on cash: 9.13% Airbnb Rental Income: $708 Traditional Rental Income: $797 Airbnb ROI: 2.84% Traditional ROI: 9.13%
931 BLACK OAK Drive Oakland, MD Very motivated sellers!!!Escape to Your Profitable Mountain Sanctuary: The Yough Mountain ...	3 beds \| 1 baths \| 990 sq.ft.	$329,999	Airbnb cash on cash: 0.94% Traditional cash on cash: 4.74% Airbnb Rental Income: $1309 Traditional Rental Income: $2082 Airbnb ROI: 0.94% Traditional ROI: 4.74%
231 SANTA FE Trail Oakland, MD 3/4BR 3BA chalet with LAKE VIEWS! 2300sf vacation home fronting on a mountain stream, over...	4 beds \| 3 baths \| 2,280 sq.ft.	$629,000	Airbnb cash on cash: 0.72% Traditional cash on cash: 1.58% Airbnb Rental Income: $2035 Traditional Rental Income: $2010 Airbnb ROI: 0.72% Traditional ROI: 1.58%

Real Estate investment in Oakland, MD

There are 100 properties for sale in the city of Oakland . The median list price in Oakland is $242,855 and the average price per square foot is $118. In August 2026, the average monthly cash on cash return in Oakland is 2.00%. The average monthly rental income in Oakland is $2,595.

Oakland, MD Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 100 investment properties available for sale in Oakland.

In 2026, the best neighborhood to buy investment property is Oakland.

The ROI for Short-Term is higher than the Long-Term in Oakland with average rental income of $1,310.

Your search for investment property begins and ends here

Investment Property for Sale in Oakland, MD

565 GLENDALE Road #306

Oakland, MD

2 beds | 1 baths | 772 sq.ft.

$249,900

Airbnb cash on cash: 1.67%

Traditional cash on cash: 5.25%

Airbnb Rental Income: $1310

Traditional Rental Income: $1747

Airbnb ROI: 1.67%

Traditional ROI: 5.25%

321 DEER PARK HOTEL Road

Oakland, MD

3 beds | 2 baths | 2,476 sq.ft.

$399,900

Airbnb cash on cash: 0.64%

Traditional cash on cash: 5.41%

Airbnb Rental Income: $1309

Traditional Rental Income: $2692

Airbnb ROI: 0.64%

Traditional ROI: 5.41%

256 JEFFREY Lane #28

Oakland, MD

3 beds | 4 baths | 1,838 sq.ft.

$464,900

Airbnb cash on cash: -0.11%

Traditional cash on cash: 5.35%

Airbnb Rental Income: $1309

Traditional Rental Income: $3281

Airbnb ROI: -0.11%

Traditional ROI: 5.35%

638 GLENDALE Road

Oakland, MD

5 beds | 3 baths | 2,640 sq.ft.

$745,000

Airbnb cash on cash: 0.48%

Traditional cash on cash: 2.49%

Airbnb Rental Income: $2422

Traditional Rental Income: $3228

Airbnb ROI: 0.48%

Traditional ROI: 2.49%

98 BEAR RUN Road

Oakland, MD

3 beds | 2 baths | 1,080 sq.ft.

$550,000

Airbnb cash on cash: 0.16%

Traditional cash on cash: 3.29%

Airbnb Rental Income: $1309

Traditional Rental Income: $2510

Airbnb ROI: 0.16%

Traditional ROI: 3.29%

25 SILVER TREE Lane

Oakland, MD

5 beds | 4 baths | 2,364 sq.ft.

$749,900

Airbnb cash on cash: 0.34%

Traditional cash on cash: 1.81%

Airbnb Rental Income: $2422

Traditional Rental Income: $2858

Airbnb ROI: 0.34%

Traditional ROI: 1.81%

55 VILLAGE Drive #5

Oakland, MD

3 beds | 3 baths | 2,280 sq.ft.

$585,000

Airbnb cash on cash: -0.34%

Traditional cash on cash: 3.66%

Airbnb Rental Income: $1309

Traditional Rental Income: $3088

Airbnb ROI: -0.34%

Traditional ROI: 3.66%

8956 OAKLAND SANG RUN Road

Oakland, MD

3 beds | 2 baths | 1,064 sq.ft.

$219,900

Airbnb cash on cash: 2.54%

Traditional cash on cash: 9.26%

Airbnb Rental Income: $1309

Traditional Rental Income: $2302

Airbnb ROI: 2.54%